Iodine → [1-(6-Chloro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 561016Notes

Reaction equation

HRID 561016 reaction equation
C([Li])(C)(C)C.[C:6]([O:10][C:11](=[O:22])[NH:12][CH:13]([C:15]1[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][CH:20]=1)[CH3:14])([CH3:9])([CH3:8])[CH3:7].[I:23]I>C1COCC1>[C:6]([O:10][C:11](=[O:22])[NH:12][CH:13]([C:15]1[CH:16]=[N:17][C:18]([Cl:21])=[CH:19][C:20]=1[I:23])[CH3:14])([CH3:7])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 807IodineHCID 86640491HCID 86640491, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 86640498[1-(6-Chloro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl esterYield 13.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add tert-butyllithium (35 mL, 59.6 mmol) to a solution of [1-(6-chloro-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester (5.1 g, 19.87 mmol) in THF (60 mL) under N2 at −78° C. After 30 min, add iodine (7.6 g, 29.8 mmol) in THF (20 mL) over 30 min at −78° C. Stir for 1 hour and then warm up to room temperature. Quench with water, extract in ethyl acetate with saturated aqueous sodium chloride, dry over Na2SO4. Purify on column chromatography 5% to 20% ethyl acetate in hexanes to obtain product (1 g). MS (ES) m/z 383 [M+1]+.

Workup

  1. customQuench with water
  2. extractionextract in ethyl acetate with saturated aqueous sodium chloride
  3. dry with materialdry over Na2SO4
  4. customPurify on column chromatography 5% to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0f38866e003547e185618ca96fc3faf9
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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